How to Pick The Proper Valentine's Day Gift

Professional Matchmaker; President of SamanthasTable.com; Founder of iPhone dating app, The Dating Lounge; Author, 'Matchbook: The Diary of a Modern Day Matchmaker'

04/14/2010 05:12am ET | Updated November 17, 2011

This post was published on the now-closed HuffPost Contributor platform. Contributors control their own work and posted freely to our site. If you need to flag this entry as abusive, send us an email.

Do you ever feel stumped when it comes to celebrating Valentine's Day and picking the right gift or card?

Here's what I know...

- Keep in mind that if you are dating someone, you need to acknowledge Valentine's Day in some way.If you try to pull the ol', "Valentine's Day is just a Hallmark holiday and I don't believe in it," you will just end up in the doghouse. Trust me.

- Valentine's Day can be a tricky holiday because you want to do enough so that you get brownie points for effort but you don't want to do too much or go over the top because that could scare someone off or give the wrong message. Doing enough means doing something, anything, even if it's stopping at the Food Emporium Supermarket on the way home and picking up candy and flowers. Doing too much means putting on the full court press for someone you barely know with flowery love cards, and dinner at the most romantic restaurant in the city like One if By Land, Two if By Sea.

- You need to give gifts and cards that are commensurate with the level of your relationship. This means that if you have only been out a few times, you need to pick a Shoebox Greeting card that is more playful, sarcastic and funny rather than mushy gushy. In this instance, mushy gushy will make things awkward and give off the wrong message. Just the same, if you have been dating a long time, you can't get away with a funny card or an impersonal card and you can't get away with just signing your name. If you have been together for awhile, your beau is going to expect a sentimental card, a Hallmark card that has script font and with a handwritten message in it from you.

- Keep in mind that women always compare their Valentine's Day gifts, cards and experiences with their friends and colleagues. The women always do a play by play for each other, so you need to step up. You definitely don't want your gal to be the gal by the water cooler who has nothing to brag about. You need to give her something to cluck over. And the water cooler winners are not always the ones who get the most expensive gift or were taken to the fanciest dinner. The admired woman by the water cooler is always the one who tells the most romantic story about her Valentine's Day evening that is met with the most "Ohhhhhs and Ahhhhs" about how sweet and adorable you were. Can you be that guy?

- Lingerie is a risky gift. A lot of men want to give lingerie to their ladies. First of all, they like seeing their gal in it and secondly, they think this is a good way to signal to their gal that they think she is sexy. However, if you are thinking of buying lingerie, make sure you are at the "lingerie" stage of your dating or the girl might get offended and think it is an inappropriate sexual overture. Equally, make sure that you pick tasteful lingerie- if you pick out a raunchy teddy straight from the pages of Hustler, your girl might think you don't respect her. You can only go with sleazy lingerie if sleazy and edgy is part of your sexual repertoire with your gal; don't use Valentine's Day to change things up.

- Make sure to choose a gift that your beau would like, not just something that you would like. For example, don't get her tickets to a Sixers basketball game rationalizing that it's a night out for the two of you and at least you get to see some basketball. Instead you should get her tickets to a Broadway show like Wicked that SHE would enjoy and you should go along with a big smile on your face. And girls, don't get him a manicure and pedicure for Valentine's Day because you think he has grody feet and you think of it as a "pampering day"; men don't find pampering to be enjoyable. Instead, buy him a day at Skip Barber race track and save the hygiene intervention for another day.

- Make sure you choose a gift that has something romantic and thoughtful about it and isn't just practical. Don't buy her a new blow-dryer because you know she needs one or a gift certificate to her yoga studio. Take the time to pick out a gift she would like and wouldn't buy herself. And think about going to yoga class with her; she will find this to be romantic

- If you can't spend a lot of money, go with a creative and sentimental gift. Some good ideas are things like a handmade gift certificate redeemable for one back massage or a gift certificate redeemable for 5 "non- veto-able" movie choices. Or sprinkle rose pedals and Hershey kisses all over the bedroom and have a bubble bath drawn in a candle lit bathroom. Or make a mix CD of all of your honey's favorite songs but remember it's about his or her favorites, not yours! Gifts don't have to be expensive to be romantic.

Samantha Daniels is a well known Professional Matchmaker, President of Samantha's Table Matchmaking and the author of Matchbook: The Diary of a Modern Day Matchmaker (Simon & Schuster).